1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 11459609, compound

HRID 1760633Notes

Reaction equation

HRID 1760633 reaction equation
Cl[N:2]1[CH2:7][CH2:6][C@H:5]([C:8]2[S:12][C:11]3[CH:13]=[CH:14][CH:15]=[C:16]([O:17][CH3:18])[C:10]=3[CH:9]=2)[CH2:4][C@@H:3]1[CH3:19].C1CCN2C(=NCCC2)CC1>C1COCC1>[CH3:18][O:17][C:16]1[C:10]2[CH:9]=[C:8]([CH:5]3[CH2:6][CH2:7][N:2]=[C:3]([CH3:19])[CH2:4]3)[S:12][C:11]=2[CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86590505HCID 86590505, compound

Product 1

HCID 11459609HCID 11459609, compoundYield 111.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the crude cis-(±)-N-chloro-4-(4-methoxybenzo[b]thiophen-2-yl)-2-methylpiperidine (2.348 g, 7.93 mmol) in THF (80 mL) was treated with DBU (1.18 mL, 7.93 mmol). After stirring 17 h, the DBU salt was filtered off through a sintered funnel, rinsed with Et2O, and the filtrate was concentrated under reduced pressure to give 4-(4-methoxybenzo[b]thiophen-2-yl)-2-methyl-3,4,5,6-tetrahydropyridine as a golden oil (2.3 g, 99%) that was immediately used in the next step.

Workup

  1. filtrationthe DBU salt was filtered off through a sintered funnel
  2. washrinsed with Et2O
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bb018ad0095642a3a8eda155aaa8acd8
Source dataset
uspto-grants-2005_01
Patent number
US06844344B2

Reaction notes

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